The Mid-Season Challenge 

Week 1 is a holiday for sportsbooks. Acquisition spikes, reactivations return, and engagement is electric. By mid-season, that initial momentum often fades. Some bettors drop off until the playoffs. Others reduce activity. The real opportunity is to turn the mid-season lull into mid-season growth by using NFL engagement as the anchor and cross-selling into other sports and casino where intent already exists. 

This is where smarter orchestration, targeted personalization, and test-and-learn decisioning become decisive advantages. 

Why Cross-Selling Works in Mid-Season 

The NFL season does not exist in isolation. By October and November, bettors have multiple sports to choose from. MLB Playoffs are in full swing. The NBA and College Basketball tip off. The NHL returns. Casino remains a steady engagement driver, especially during off days and between games. Operators who use NFL activity to deepen engagement across verticals outperform those who ride a single-season wave. 

As our VP of Customer Success, Americas Sam Zerfoss noted on The Gambling Files podcast, the U.S. market is maturing. Operators are getting smarter about how they use AI decisioning, testing frameworks, and personalization to keep “fickle fans” engaged. Instead of over-relying on blunt promotions that drive short-term spikes, the leaders are orchestrating the right offers to the right bettors at the right time, across channels, sports, and products. 

Tune into The Gambling Files podcast, featuring Sam, to hear more: 

Our Director of U.S. Sales Jeff Laniado adds that sportsbooks are largely commoditized from a bettor’s perspective. If a bettor wants to wager on a game tonight, they often have multiple apps to choose from with similar odds. Differentiation comes from two places: superior product and user experience, and smarter CRM powered by segmentation, orchestration, and targeted offers. As an example, Jeff cited a major sportsbook operator crediting a 37% increase in handle per active user to smarter segmentation and more surgical promo targeting. That is the kind of uplift operators can unlock by focusing on CRM as a core growth lever, not just a support function. 

How to Execute a Mid-Season Cross-Sell Strategy 

Below are six different tactics to reduce churn:

1. Build personalization in layers 

Sam breaks personalization into four practical layers that top operators use now. Jeff reinforces that these layers are the difference between generic mass offers and measurable uplift. 

• Segmentation: Group bettors by behaviors and propensities such as NFL-only bettors, parlay-driven bettors, or multi-sport bettors. Identify high-propensity cohorts likely to convert on the next-best action 
• Campaign selection: Choose the right top-line narrative for each cohort. For example, when to push NBA tip-off vs. MLB Playoffs vs. casino tie-ins for NFL cohorts 
• Channel and offer selection: Deliver on the bettor’s preferred channel and with the right bonus type and depth. Not everyone needs the most generous bonus. AI decisioning can match the right offer type (free bets, deposit match, no-deposit, odds boost) to each bettor to maximize uplift and minimize waste 
• Last-mile content: Tailor copy and creative to the person. Align imagery to team affinity when appropriate, but Jeff cautions against blindly pushing favorite-team bets. Many fans avoid betting on their own team or hedge in the opposite direction. Behavior often reveals different preferences than fandom alone 

2. Orchestrate, do not flood 

Mid-season is when overlapping eligibility explodes. A single bettor might qualify for multiple offers based on balance, parlay results, team affinity, tenure, recency, or tier thresholds. Without orchestration, operators risk sending four or five campaigns to the same person in a day and creating fatigue. 

Orchestration uses AI decisioning to prioritize the campaigns that create the highest incremental impact. Jeff emphasized that moving from static segmentation to orchestrated delivery is how operators create the kind of per-user gains cited above. It is the difference between sending everything and sending the right thing. 

3. Test, measure, and manage fatigue with incrementality 

To know whether a campaign engages or annoys, Jeff recommends rigorous test vs. control measurement. Hold out a statistically valid control group, then measure true incrementality on the right KPI. Sometimes you will see uplift in NGR but not in GGR. Other times deposit frequency rises but average deposit declines. Pick the metric that matters for each campaign and let the data show where the line is between helpful and intrusive. 

Jeff also recommends monitoring message frequency by player. Different players have different thresholds and different channel preferences. Some tolerate two emails a day. Others do better with mobile push and in-app messaging. Use data to tune frequency and channel mix to reduce fatigue while increasing conversion. 

4. Use the mid-October window as a cross-sell inflection point 

Sam highlighted a key moment in the calendar. Mid-October is a natural cross-sell inflection point because of overlapping seasons: 

• MLB Playoffs 
• NBA and College Basketball tip-off 
• NHL returns 

Use this window to test which adjacent sports each NFL bettor is most likely to engage with next. Run experiments at scale to identify the best path for each bettor, then deepen engagement over time with tailored offers. 

5. Cross-sell into casino with machine learning 

Casino is the year-round cross-sell engine, but it must be introduced intelligently. AI can predict which casino experience each bettor is most likely to try first, rather than blasting a generic blackjack offer. Jeff points out that doing this manually is not feasible at scale. Machine learning makes it targeted and efficient, especially when the operator wants to introduce casino to NFL bettors during non-game windows. 

6. Meet bettors where they are: mobile 

Mobile is the primary device for betting. In Optimove research discussed on the podcast, 76% of bettors prefer to place bets on mobile. This should shape timing and channel strategy: 

• Time mobile pushes closer to kickoff for mobile-first bettors. 
• Shift toward email or web for bettors who typically wager on desktop. 
• Use geo-targeting to trigger timely messages when a bettor enters a stadium or a sports bar. If a bettor walks into MetLife Stadium on a Sunday, that is a timely moment to trigger a relevant push. 

Knowing who prefers which platform reduces noise and increases conversion, especially in mid-season when attention is fragmented across sports. 

Positionless Marketing: The Advantage in Mid-Season 

Executing mid-season cross-sell across verticals, channels, offers, and creative at scale requires teams that can move without friction. This is where Positionless Marketing provides a structural advantage. It empowers every marketer to act independently across the full lifecycle so they can move from insight to execution in real time: 

• Data Power to identify the right cross-sell segments and moments 
• Creative Power to generate channel-ready assets tailored to the sport and bettor 
• Optimization Power to orchestrate and self-optimize campaigns across channel and cohort 

This is how operators keep pace with bettors through the middle of the season when execution speed and decision quality matter more than headline offers. 

The ROI of Smart Mid-Season Strategy 

While blunt promotional strategies might drive short-term activity, the sophisticated approach outlined here delivers compounding returns. Operators implementing AI-driven orchestration and cross-selling typically see: 

• Higher lifetime value through expanded product engagement 
• Improved retention rates by maintaining year-round touchpoints 
• Better promotional efficiency through targeted rather than mass offers
• Reduced acquisition costs by maximizing existing player value 

The example of 37% handle increase per active user demonstrates the scale of opportunity available to operators who prioritize intelligent CRM over volume-based marketing. 

In Summary

The middle of the NFL season is not a slump. It is a cross-sell moment. Operators who combine AI decisioning, segmentation, orchestration, experiment-led measurement, and creative incentives will sustain engagement and expand player value into adjacent sports and casino. As Sam Zerfoss emphasized, the market is maturing. As Jeff Laniado reinforced, the leaders are not just acquiring more. They are personalizing smarter, orchestrating better, measuring incrementality, and acting in real time. 

That is how to convert Week 1 excitement into sustained growth through the Super Bowl and beyond. 

For more insights on player churn, contact us to request a demo.

Published on September 23rd, 2025

Posted in

• Marketing AI
• Gaming
• Personalization

Rob Wyse

Rob Wyse is Senior Director of Communications at Optimove. As a communications consultant, he has been influential in changing public opinion and policy to drive market opportunity. Example issues he has worked on include climate change, healthcare reform, homeland security, cloud transformation, AI, and other timely issues.